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Her First Time, Like It or Not (I did)

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2005-08-15

Tom and I had been good friends since college. He had married a really hot girl we went to college with, Beth, that I had a hard time not lusting over. Alright, I had tried to sneak a few peaks of her naked when we vacationed together, but unfortunately always failed. The years went by and they quickly had two daughters, while I stayed single. Tom and I remained friends, but it seemed he and beth kept getting more uptight with the years.
Their oldest daughter, who had turned 18 in June, was named Molly.
Molly always had a slender build and was average height, I am guessing about 5 foot 4 inches. At her 14th birthday party I noticed she was starting to develop, probably up to a solid A cup, if not a small B cup. She still had a slender build, but with her very tiny waist could not help noticing that she had the hour glass figure well on its way.  
Molly and I always got along well. The fact that I had a ski boat and would have her family down for weekends at my cottage did not hurt. While her parents were relatively strict with her and treated her like a little kid I tried to build her up and complement her on her beauty. With her light brown hair, big blue eyes and cute body the compliments were not fake.
It was during one of these planned weekends at the lake cottage that Molly and I unexpected spent some time alone. Molly had been at cheerleading camp all week near my lake cottage and I volunteered to pick her up that Friday afternoon and take her to the cottage, since Tom had to work a full day and then go home to pick up the rest of his family.
Even though I was in my mid thirties the thought of stopping by a cheerleading camp and then spending an hour in a car with Molly was pretty enticing.

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   I was on my way to pick up Molly when I recieved a cell phone call from her mother Beth. It ends up Molly's little sister had try outs for a play she really wanted to be in the next morning so they could not make it to the cottage until noon on Saturday. She apologized and offered to drive out that night to get Molly. I told her not to bother, that I would just take Molly straight to their place or Molly could just spend the night. Beth said she did not want to inconvenienceme and I said it was zero inconvenience since I was just planning to do some work on the cottage and the boat. We agreed to leave it up to Molly and touch base after I picked her up.
The cheerleading camp was as much fun as  I thought it would be. I was early, as planned, and there were babes everywhere. The camp was for high school age cheerleaders, and some of the older girls looked like they could be LA Laker dancers. Some of the girls were really built, and I was thinking they must really bounce when they jump. Found Molly and she gave me a big welcome hug, which I made sure to extend by pulling her tight. Helped her load her stuff and noticed her body looked even tighter after a week of working hard at the camp. Her blue eyes really stood out as her skin had darkened from being in the sun.
As we were pulling out I gave her the news about her families delay and gave her her options, drive two hours back home or drive a half hour to the cottage and go water skiing. Wanted to frame the question right and it worked.

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   After she gave me the no duh look she called her mom and told her she wanted to go to the cottage. I over heard her mother tell her to make sure she helped me clean the cottage and boat.  
We arrived at the cottage and it was in great shape, after my sisters family hd borrowed it the week before. The boat though definitely needed cleaning, after sitting on a trailer for the last month. Molly said she would clean it, but I told her I could not let her do it alone. She then realized that she was without a bathing suit, in that her mother was suppose to bring one for her. After a few dirty thoughts crossed my mind (like tellg her she did not need one) I remembered that my sister kept a suit at the cottage.
I gave Molly the suit and a safety pin, since my sister, while thin, was bigger than Molly. Molly came out in the bikini top, with her cheer shorts on over the bikini bottoms. She grabbed a sponge and asked where to start. My sick mind worked quickly, and I  told her it would be easiest for her to start on the outside of the boat, since she could stand up while working. I told her I would work along with her from the inside of the boat reaching down to the areas she could not reach. While she thought I was being nice, I knew I was just being a pervert in that with this arrangement I would be forced to be looking down at her beautiful hard body the whole time we worked.
I wondered if other people my age were anywhere as close to being this sick, in that Molly was only 18 and I am twenty years older.  But at that point I did not care, she looked great and I was rock hard.

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   We begin working. the too large bikini top was was a huge fringe benefit, in that it would just hang open when Molly bent forward to get more water on her sponge. She would often try to hold the top to her chest when she would bend over, but with a sponge in one hand and her other hand all wet she would often fail and it made for a great show.
It was interesting, with a bra on Mollys breast looked small and round, but when hanging loose they looked like small pyramids, sticking straight out. Her nipples were lightly colored and also seemed to be sticking out hard. I was thinking maybe it was from the cold well water. We had only been at the cottage and hour and  I could not believe I had seen Molly's beautiful breast, even if she was trying to hide them. Never enjoyed cleaning the boat more and was sad when we were done, thinking it might be the last time I ever saw breasts that young and perfect.
Told Molly I felt bad making her work that hard and offered to let her water ski. She jumped at the chance and I let her ski until she was exhausted. During her other visits she just had short turns, since there were always others waiting. She could not believe I kept letting her go again and again after she would fall.
The highlight for me was holding the ladder in place as she climbed on board after her last ride. She was worn out and it was a struggle to pull herself up the ladder. The bikini bottom had stretched a bit after getting wet and the safety pin did not stop it from sliding a few inches down her butt as she climbed out.

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   What a sight, that beautiful white tight butt, just below the dark tan line. Could have looked forever, but seeing that she was struggling had to move around to her front to help pull her out.
Went back to the house and both showered and got dressed for dinner. I grabbed a beer and she was having a lemonade. Molly came in wearing a short jean skirt and a tight while tank top, clothes I knew she would not be wearing if her parents were present. I mentioned how beautiful she was and asked if she was dating. She mentioned that she was not allowed to date until she was 18 I asked if she ever had a boyfriend and she said no. She said her friends had told her about boys that liked her, but between going to a Catholic grade school and her parents rules it was not possible to have a boyfriend. I told her that would change quickly now that she was going into high school and that I would have asked her out in a second. She giggled and said she was a bit afraid of the whole dating thing, since she had zero experience.
Joking around I said I would be her boyfriend that night at dinner, so that she would be at least a little prepared. She looked at me and said that would be fun. I said "ok, but this is just betwen you and I and don't make fun of me if I stutter, because I am not used to such a beautiful girlfriend. " She punched me in the arm and said to quit teasing and I responded that I was not teasing. Molly left to grab a sweater, I ws hoping she would not put it on over her tank top.

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I grabbed another beer and a lemonade for Molly. This is where I really began to cross the line for the first time. I put a little extra dry lemonade mix in Molly's glass and a small shot of vodka. Don't really know what I was thinking, but thought it would make things interesting. Also put another few shots of vodka in a zip lock bag and put it in my pocket. I knew what I was doing was way wrong, but ever since seeing those gorgeous firm breast jutting out earlier I was thinking all day with the wrong head.
Molly returned and I toasted the new couple. I told her I would treat her like a girlfriend and show her the things boys would try on dates. I said boys would probably try to move things along faster than her and she needed to be ready and to figure out how she would respond. I repeated that this was favor to her and that it was just between us and she said of course.   We finished our "cocktails" and I grabbed her hand for the walk to the car, it felt so smooth and small.
The restaurant was very nice, with a pretty view of the water and sunset. We sat next too each other facing the water. Molly was very talkative and relaxed, I think her first shot of alcohol had her initially flying. When she left the table to visit the rest room I snuck a secong vodka shot into her drink, and decided that was enough if not too much.

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When she came back I told her she would be pretty safe in a restaurant, but in a secluded table like this a boy might let his hands wander. She looked at me like "what are you talking about?". I said they might put their hands on her beautiful leg and just hold it or slide their hands up and down like this and showed her with my hand just above her knee. She said "that does not seem to be too bad". I said it is not, but with her wearing a short skirt they might try to push it a little further and slide their hands up her skirt a little and I then slid my hand a lttle under her skirt and massaged a ways up her thigh before pulling out (boy did she feel great). She said why would they do that. I could tell she was not playing dumb, so I slowly described the steps boys might take using the old baseball analogy. First base = kiss, second base = touching breasts. . . I used very tame language and said it was awkward to discuss but she should know what her friends are talking about and how boys think. Don't know if she bought it all. At this point dinner was over and it was time to head home.
On the drive home I mentioned that dates often consisted of a dinner and movies, and we could watch a movie at my house. Molly said she was game.

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    We got home and I said Molly could pick a movie. She was looking at an r rated movie and said it looked good but her parents would never let her watch it. I said go ahead, since I knew it had a few very sensuous scenes.
I grabbed us another round of drinks, beer for me and a lemonade surprise for Molly. I made another toast to a great first date. Molly was getting glassy eyed and was swaying a little at this point. I took her by the hand and sat her down next to me I wrapped an arm around her shoulder and told her that is how dates often sit. I looked down at her beautiful eyes and could tell she was not all there, perhaps I had gone alittle heavy on the vodka. I told her to just rest her head on my shoulder and relax.
After a few minutes of the movie I told her this was probably the first move many boys would take and I slowly moved my right hand down from her shoulder to the closest breast and gave it a nice slow feel and just left it there (they were small, but as firm as my imagition had thought). For a split second I thought she was going to leave my hand alone, but even in her condition she reacted and pushed my hand a way. I told her that with her beautiful face and great body boys would be trying that often and she would have to decide when she was ready. I asked her how it felt "good, bad. . .

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  ", and she said it just felt weird. So much for my ability to turn on a fourteen year old.
I then said at this point boys would often try to go for a kiss.   I asked her if she had ever kissed before and she said only relatives. I aksed her to show me and she gave me a peak on the cheek. I told her boys would want it longer on the mouth and she gave me a longer closed mouth peck on lips. I then gave her an explanation of the different types of kissing, from pecks on the hand to deep french kissing (DFK) with tongue play.
I told her to save the DFK kissing for a boy she really liked, but that she should really practice before that time. I said lets try it real slowly and at least you will know what to do. She gave me a doubtful look but softly said ok, perhaps the vodka was helping me. We started lightly kissing, with her mouth open about 1/16 of an inch. I explained that was not quite it and told her to kep her lips loose and  I would show her. I slowly pushed her lips open with my tongue and tried to be very gentle and slow, so that she did not get spooked. I gently kissed her top and lower lips, which were incredibly soft. She felt great, but there was little coming back.

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   I then explained that she would need to kiss back more, but that it would be easier with a real boyfriend. I said lets rest for awhile and we can practice some more later.
I was hard as a rock, to the point where it almost hurt. Here I had my arm around a beautiful young lady, with a tight 95 pound body and nubile firm young breasts. I looked down and Molly had her eyes closed. She appeared to be sleeping, but was probably half passed out. I sat like that for a few minutes, wondering what I should do. Part of me thought I should just go to my room and whack off, so that this situation did not get anymore out of control. However, the other head won the battle.  
I lifted Molly's thin arm and dropped it, it just fell limp. She was really out of it. I softly turned her head towards me and went in for a kiss. Her soft lips were slightly parted, and I just kissed her like that. Then I slowly worked my tongue into her pretty warm mouth. Still not much reaction, just some warm air coming out of her nose.

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I then reached down and started lightly massaging her left breast with my hand. I slowly massaged a little harder, trying to see if I could feel her nipple start to harden. Just as I thought I could feel her nipple harden a little Molly began to shake her head, trying to break off our kiss. She was back awake, but looked a little out of it.
Molly asked, "what are you doing?". I said remember I said we were going to practice kissing a little more, and she shook her head yes. I then told  told Molly that one of my favorite moves, and one that boys would try often, was to slowly reach down and touch a girls breast while kissing.  I said that when boys did that they would often try for more that just a quick feel through a shirt like I just did. Molly gave me a "what our you talking about?" kind of look. I said let me show you and I gently kissed her on her lips and she slowly let my tongue open her mouth, but again she was not really kissing back.
I continued to kiss her gently, hoping not to spook her. I slowly worked my hand from her back to the bottom of her tank top.  The skin on her stomach was soft, but her stomach muscles were very tight. I slowly slid my hand up and had it on top of her bra, but under the tank top. Her bra material was very soft and had no seams.

 

   Still I could not find her nipple through the material before Molly pulled my arm down.   
After that rejection I told Molly that when kissing boys might try to grab her breast through her shirt or bra, or they might really go for it. Molly said I think I know what you mean, but I think we have done enough for a first date and I need to go to bed. She was right, we had done way to much. However, at this point I was one step beyond hard and could feel some pre cum wetness in my pants. I was so exited I was in pain.
I knew I had pushed our little game as far as Molly wanted and could tell by her eyes that she was not interested in going any further, but I also knew I could not stop with a quick touch of her breasts through a bra at this point. I said "ok Molly, you are probably right. Let's take a break from our date and get a little sleep. " I gently pushed her head back on my shoulder and told her I wold walk her to bed in a minute.
Walking Molly to her bed to sleep was one of the last things I wanted to do. After a few minutes Molly fell asleep (or passed out) again. I waited another ten minutes, picked up the light little girl and carried her into the guest bedroom. I dropped Molly on the bed and just looked at her. She had a beautiful face, with long brown hair.

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   Her cheekbones were those of a model. Her shoulders were wide and thin. Her chest was not big, but she was so thin it looked perfect. Her waist had to be under twenty inches and her legs were thin but defined. I loved thin legs.
I could of, and probably should of, left at this moment, but there was no way I could. I had to really touch and see those beautiful little tits up close. I layed down next to Molly and pushed her hair out of her face. I leaned over and lightly kissed her. I then slowly slid my hand up her shirt. No reaction at this point, still asleep. I gently felt around the front of her bra, damn! it was not a front snapping one. So I very carefully strated sliding her bra over one breast.  Luckily her breasts were relatively small and the bra pushed up rather easily. I very lightly massaged the whole breast and then starting massaging her nipple with my thumb abd index finger.

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   I thought at this point she might be passed out for the night and I could just whack off feeling her tight little body. But Molly suddenly stiffened and twisted her head to break off our kiss.
She yelled, "what are you doing?". I said "just like I promised I am showing you what a boyfriend and girlfriend do when they are in love". I was lying, of course, but was thinking she might buy it in her drunken state.  
I bent back down and started kissing Molly again. Perhaps I was thinking she never said to stop, so as long as we were kissing I had the go ahead. Her mouth was closed and she was not kissing back, but she was also not activiely trying to break the kiss off. Is that a sign to go ahead?
I quickly slid my hand back up the tank top and found her firm pointed breast. Molly's little tit felt great and I kept massaging it even as she was now trying to slide away from me and break off our kiss. So much for the go ahead.
I quickly rolled on top of her, putting my leg between her legs so that she could not slide out. I pushed up her tank top, so that her bra and one nipple were exposed. Even as I was kssing I had to take a glance down to see the beautiful sight. I began to tweak Molly's nipple, thinking it would get hard quickly, but it took a while to get it as hard at it looked when we were washing the boat.

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Now my rock hard cock was resting on her thigh, and her squirming around was grinding it through my pants. I reached down with my other hand, pushed up the bra and grabbed her other breast, it felt as great as the first. Molly was struggling to break off contact anyway she could, but 95 pounds is no match for 185 pounds, especially when that person is more sexual excited that he has ever been.
I need to taste the most beautiful breast I had ever seen, and have now touched. I slide down to kiss Molly's breasts, my waist now between her legs, pinning her down. As soon as I break the kiss, Molly starts screaming "stop, what are you doing, no. . . . . " and pulls down her shirt. I push up her shirt and look at her great little breast and start sucking on the right breast. I can get the whole breast in my mouth, and twirl my tongue around her nipple. I have to suck hard and hold her with both hands to keep contact. I am  thinking this must feel good to her, my girlfriends love this move, but the screaming reminds me that she does not enjoy it in the least.

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   I normally could do this for a long time, but not in these conditions.
I move back up and start kissing Molly again. Her mouth is closed, but I force it open with my tongue.   I am surprised I can get my tongue in her mouth and it is a lot nicer without the noise. My left hand quickly moves from the back of her head to her thigh. Molly's short skirt has ben pushed up already so it is real easy to reach the front of her panties. I start massaging her opening through the panties. Molly is trying to move away in every direction, but between my legs and arms I have her very securely positioned. Molly is not wet at all through her panties, which reminds me how far I have crossed the line and how different this is from all my previous recipricol sexual escapades.  
I move my index finger to one of Molly's long thin legs and slip it under her panties, I start moving around and find soft thin hair covering her mound.   It takes a little while, but I find her opening. It is not very wet either. I gently massage all around the opening, paying extra soft attention to her clit. I am thinking she must find this enjoyable, but look into her eyes and can tell she is not yet enjoying this encounter.
For the 20th time that night I think of stopping, knowing I should, but I am now out of my mind.

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   My hand pulls away from her warm box, but instead of stopping reaches for my zipper. I don't even thinking of stripping our clothes off, I need to be inside of Molly now! I get my zipper down quickly, but with one hand it takes a while to get my rock hard boner through my boxers. It is so hard and hot the fresh air feels good on my cock. I am almost seven inches long, but pretty thin. I remember thinking at the time that being thin was probably good for a change.  
I now reach again with a few fingers under Molly's panties. I slowly massage her opening again, but this time try to slide a finger a little inside her. I finally find the exact opening and try to push my index finger in. It slides in a little, but even trying to slide in a little is really tight. I push it up and down just an inch or so and it feels like her body is being lifted up by my finger her pussy is so tight. I now move my cock near her opening, keeping my index finger in as a placeholder.  
At this pint Ibreak off the kiss, because I want to give the next move all my attention. Molly is now really screaming "No, please stop. Anything, but this. .

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  . " But it is this or nothing for me.   I slowly start to pull out my finger and try to push my cock head in.   It does not go in at all. Did I slide away from the opening? I reach down and push in my finger - no, still got the right spot. Now I push my cock head hard and it goes in a little, which brings a huge scream from Molly. I am wondering if I am going to get all the way in and whether I am going to  explode before getting there. I begin to lightly push in and out slowly working the head in, to more screams from Molly. It is now firmly in and I run into the hard barrier I knew I would find. I feel real guilty at this point, but know I  can't stop. I give it a few hard pushes and break through, to an ear splitting scream from Molly. I am now most of the way in and want to be all the way in.  I continue with slow but firm pistoning and make it all the way. I am surprised, her pussy is so tight it feels like my cock is sliding between hard bones. It is not the wet sloppy sliding in and out that I get with my girlfriends, but instead sliding a little in either direction causes a lot of friction and almost pain to my cock.

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   I have only been inside Molly for about a minute or so, but am about to erupt. Decide to push all the way in and rest in her warm hole, so that I can savor what may be the tightest little fuck I have ever had.  
Molly is now just moaning under me.  Not fighting to get way anymore, but more of a weird whining sound is coming from her. I plan to just lay buried ddep inside her, but her pussy is alive, contracting around my cock. she is also moving a little underneath me, causing more friction. I think for a split second she is begin to enjoy this, but then realize she is just trying to slowlyly slide away from me.
I am not going to have any of that, so I reach under her to grab that tight little ass. And what a tight little ass it is, I can grab the whole thing in one hand and stilll feel her litle butt bone. This is great. I hold steady on my knees and elbows and start pistioning her up and down underneaeth me using her butt. She is really wimpering now, and  I realize  I am not going to last much longer and pull her up and down quickly a few more times before pulling out and shooting the biggest load of my life on Molly's flat stomach and chest.
It felt great as it kept shooting out and out. But immediately I look at Molly and think what  have  I done. Even crying she is beautiful and now has cum on her dark tanned stomach and bright white tits.

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   She has a weird expression on her face and does not say anything. I tell her I will grab a towel to clean her up and will be right back.
By the time I clean myself up, get a warm wet wash cloth and towel Molly is passed out again. Man, does she look hot laying there half naked, I never even took her skirt off. I start to get hard again, but realize I better stop. Even though it is tough to look at that little mouth and wonder what it would look like with a 34 year olds cock in it. I somehow fight the urge this time and quickly clean Molly up and slide her clothes back on. I can only wonder what is going to happen in the morning, but for now I have the memory of a lifetime.
.

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